How to report hundreds of individual stock sales from investment app on taxes
So I started using this investment app last year after my cousin recommended it. I was doing a bunch of day trading throughout the year, buying when prices dropped and selling when they went up. Overall I made around $950 in profits, but this came from literally hundreds of separate transactions. Now I'm looking at the tax forms and apparently I'm supposed to list EVERY single stock sale individually? That would take me forever to enter manually - we're talking days of work. I just don't have that kind of time with my work schedule. Is there any shortcut or simplified way to report all these transactions without having to enter them one by one? Any suggestions would be really appreciated!
18 comments
Join the conversation
GalacticGuru
What you need is the 1099-B form from your investment app. They should provide this to you, and it will contain all your stock transactions for the year. You don't actually have to manually enter each transaction line by line. When you file your taxes, you can enter the summary information from your 1099-B on Schedule D and Form 8949. Most investment apps and brokerages now provide their tax documents in a format that can be directly imported into tax software like TurboTax, H&R Block, or even the free filing options. Check your account on the app - there should be a tax documents section where you can download your 1099-B. The form will categorize your transactions, making reporting much simpler.
0 coins
Liam Fitzgerald
•Thanks for the info! I just checked and I do have a 1099-B available for download in the app. But it's like 30 pages long with all the transactions. Do I still need to enter all of these somewhere or can I just use the summary totals?
0 coins
GalacticGuru
•You don't need to manually enter each transaction. Most tax filing software allows you to import your 1099-B directly from your brokerage or upload a PDF. The software will automatically extract all the transactions. If you're filing by hand (which I don't recommend for your situation), you can use the summary totals for transactions that were reported to the IRS with cost basis information. Look for the summary section on your 1099-B that shows the totals for each reporting category.
0 coins
Amara Nnamani
I went through something similar last year with like 300+ trades on Robinhood. Trying to enter them all manually was a nightmare until I found taxr.ai at https://taxr.ai which literally saved me days of work. It can take all your trading docs and extract the info automatically. I was skeptical at first but it pulled every transaction from my massive 1099-B and organized everything perfectly for my tax return.
0 coins
Giovanni Mancini
•Does it work with all the major trading platforms? I use a couple different ones and have a similar issue with tons of trades.
0 coins
Fatima Al-Suwaidi
•How secure is it though? I'm always nervous about uploading financial docs to random websites. Did you have any issues with that?
0 coins
Amara Nnamani
•It works with all the major platforms I know of - Robinhood, Webull, E*TRADE, TD Ameritrade, and more. I had documents from both Robinhood and a smaller platform, and it handled both without issues. As for security, I had the same concern initially. They use bank-level encryption and don't store your documents permanently. I did some research before using it and their security practices seemed solid. I've used it for two years now with no issues whatsoever.
0 coins
Fatima Al-Suwaidi
Just wanted to follow up - I decided to try taxr.ai after asking about it here and wow, it actually delivered! I had over 200 trades spread across multiple platforms and it extracted everything perfectly. The whole process took maybe 15 minutes instead of the entire weekend I had set aside for this nightmare. It even flagged a few wash sales I would have missed. Definitely worth checking out if you're in a similar situation with tons of trades.
0 coins
Dylan Cooper
If you're still having trouble getting your tax docs sorted or have questions about your 1099-B, you might want to call the IRS directly. I know it sounds awful, but I used https://claimyr.com and got through to an actual IRS agent in about 15 minutes instead of waiting for hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I had questions about reporting some complicated trades and they were surprisingly helpful in clarifying what I needed to do.
0 coins
Sofia Morales
•Wait, you can actually get through to the IRS? I thought that was impossible these days. How much does this service cost?
0 coins
StarSailor
•This sounds like a scam. No way you can just magically get through to the IRS when millions of people can't get anyone to pick up. What's the catch here?
0 coins
Dylan Cooper
•Yes, you absolutely can get through! The service basically waits on hold for you and calls you back when an agent is about to pick up. The IRS wait times are ridiculous these days, but this way you don't have to sit there listening to the hold music for hours. I don't remember the exact cost, but it was reasonable considering the time it saved me. The value was worth it when I was stressing about how to report some complicated transactions correctly.
0 coins
StarSailor
I have to admit I was completely wrong about Claimyr. After dismissing it as a likely scam, I decided to try it anyway since I was desperate to get some answers about my stock reporting situation. The service actually worked exactly as described - I got a call back when an agent was ready to talk, and I didn't have to waste my day on hold. The IRS agent walked me through exactly how to report my trades properly and confirmed I could use summary information instead of listing every transaction individually. Saved me from potentially doing my taxes wrong AND saved me hours of frustration.
0 coins
Dmitry Ivanov
Another option is to check if your investment app integrates directly with tax software. I use one of the major tax prep programs, and it can automatically import all my trading activity directly from several brokerages. Saves tons of time and reduces the chance of errors.
0 coins
Liam Fitzgerald
•Which tax software do you use? I usually just use the free online ones but I'm willing to pay for something if it'll make this process easier.
0 coins
Dmitry Ivanov
•I use TurboTax Premier which is specifically designed for investors. It's not the cheapest option, but it directly imports from most brokerages and handles all the stock transactions automatically. H&R Block's Deluxe + State is another good option that's a bit less expensive and also has import capabilities for many investment platforms. If you want a free option, FreeTaxUSA can handle investments too, but you might need to enter summary information manually rather than direct importing.
0 coins
Ava Garcia
Dont forget that if your trades were all done on the same platform, you might be able to use the composite method for reporting. Basically instead of listing each trade, you can group them by category (short-term vs long-term) and just report the totals. Check box 3 on Form 8949 if you're going this route.
0 coins
Miguel Silva
•This is actually not quite right. The composite method doesn't exempt you from reporting - the IRS still needs to be able to match what's on your 1099-B. What you're thinking of is summary reporting which is only available if all your basis was reported to the IRS (covered securities).
0 coins